Arvia • P&O Cruises
14-night Southern Caribbean Loop via Fort-de-France, Basseterre, Saint Kitts & Philipsburg
Dec 18, 2026 → Jan 1, 2027 • Bridgetown ↔
From $3,107
$222/night
Priced high
↑21% above typical
View by
638 total
Norwegian Viva • Norwegian Cruise Line
7-night Southern Caribbean Loop via Basseterre, Saint Kitts & Castries
Jan 23, 2028 → Jan 30, 2028 • San Juan ↔
From $1,064
$152/night
Priced high
↑21% above typical
Iona • P&O Cruises
14-night Eastern Caribbean Loop via Basseterre, Saint Kitts, Tortola & Philipsburg
Dec 25, 2027 → Jan 8, 2028 • Bridgetown ↔
From $2,742
$196/night
Priced high
↑21% above typical
Emerald Princess • Princess Cruises
5-night Eastern Caribbean Arc via Saint Thomas & Philipsburg
Nov 21, 2027 → Nov 26, 2027 • San Juan → Bridgetown
From $744
$149/night
Priced high
↑20% above typical
Iona • P&O Cruises
14-night Eastern Caribbean Loop via Basseterre, Saint Kitts, Tortola & Philipsburg
Nov 13, 2027 → Nov 27, 2027 • Bridgetown ↔
From $2,161
$154/night
Priced high
↑20% above typical
Iona • P&O Cruises
14-night Eastern Caribbean Loop via Basseterre, Saint Kitts, Tortola & Philipsburg
Nov 26, 2027 → Dec 10, 2027 • Bridgetown ↔
From $2,161
$154/night
Priced high
↑20% above typical
Rotterdam • Holland America
21-night Western Caribbean Loop via Half Moon Cay, Falmouth & Cozumel
Dec 12, 2026 → Jan 2, 2027 • Fort Lauderdale ↔
From $2,799
$133/night
Priced high
↑20% above typical
Britannia • P&O Cruises
14-night Southern Caribbean Loop via Philipsburg, Antigua & Basseterre, Saint Kitts
Feb 5, 2027 → Feb 19, 2027 • Bridgetown ↔
From $2,742
$196/night
Priced high
↑19% above typical
Norwegian Prima • Norwegian Cruise Line
7-night Eastern Caribbean Loop via Tortola, Basseterre, Saint Kitts & Bridgetown
Jan 10, 2027 → Jan 17, 2027 • San Juan ↔
From $1,499
$214/night
Priced high
↑19% above typical
Norwegian Prima • Norwegian Cruise Line
7-night Eastern Caribbean Loop via Tortola, Basseterre, Saint Kitts & Bridgetown
Jan 24, 2027 → Jan 31, 2027 • San Juan ↔
From $1,499
$214/night
Priced high
↑19% above typical
Crown Princess • Princess Cruises
7-night Southern Caribbean Loop via Philipsburg, Fort-de-France & Saint George's
Jan 17, 2027 → Jan 24, 2027 • San Juan ↔
From $969
$138/night
Priced high
↑19% above typical
Iona • P&O Cruises
14-night Eastern Caribbean Loop via Basseterre, Saint Kitts, Tortola & Philipsburg
Nov 12, 2027 → Nov 26, 2027 • Bridgetown ↔
From $2,134
$152/night
Priced high
↑19% above typical
MSC Seaview • MSC Cruises
7-night Southern Caribbean Loop via Pointe-à-Pitre, Castries & Bridgetown
Feb 20, 2027 → Feb 27, 2027 • Fort-de-France ↔
From $1,204
$172/night
Crown Princess • Princess Cruises
7-night Eastern Caribbean Loop via San Juan, Saint Thomas & Philipsburg
Mar 5, 2027 → Mar 12, 2027 • Bridgetown ↔
From $1,194
$171/night
Priced high
↑18% above typical
Britannia • P&O Cruises
14-night Southern Caribbean Loop via Philipsburg, Antigua & Basseterre, Saint Kitts
Nov 13, 2026 → Nov 27, 2026 • Bridgetown ↔
From $2,134
$152/night
Priced high
↑17% above typical
Emerald Princess • Princess Cruises
7-night Eastern Caribbean Loop via Saint Thomas, Philipsburg & Antigua
Nov 21, 2027 → Nov 28, 2027 • San Juan ↔
From $1,002
$143/night
Priced high
↑16% above typical
Grandeur of the Seas • Royal Caribbean International
7-night Eastern Caribbean Loop via Charlotte Amalie, Saint Thomas, Frederiksted, Saint Croix & Philipsburg
May 29, 2027 → Jun 5, 2027 • San Juan ↔
From $942
$135/night
Priced high
↑15% above typical
Valiant Lady • Virgin Voyages
7-night Southern Caribbean Loop via Philipsburg, Bridgetown & Castries
Jan 16, 2027 → Jan 23, 2027 • San Juan ↔
From $1,113
$159/night
Priced high
↑14% above typical
Norwegian Prima • Norwegian Cruise Line
7-night Eastern Caribbean Loop via Tortola, Basseterre, Saint Kitts & Bridgetown
Feb 21, 2027 → Feb 28, 2027 • San Juan ↔
From $1,439
$206/night
Priced high
↑14% above typical
Britannia • P&O Cruises
14-night Southern Caribbean Loop via Philipsburg, Antigua & Basseterre, Saint Kitts
Feb 6, 2027 → Feb 20, 2027 • Bridgetown ↔
From $2,607
$186/night
Priced high
↑13% above typical